US2018301640A9PendingUtilityA9

Organometallic compound and organic light-emitting device including the same

Assignee: SAMSUNG ELECTRONICS CO LTDPriority: Jun 23, 2014Filed: Jun 23, 2015Published: Oct 18, 2018
Est. expiryJun 23, 2034(~7.9 yrs left)· nominal 20-yr term from priority
H01L 51/5012C09K 2211/1044C07F 15/0033H01L 51/0085C09K 11/025C09K 11/06C09K 2211/185C09K 2211/1007C09K 2211/1059H10K 50/12H10K 85/342C09K 2211/1029H05B 33/14H10K 50/11
31
PatentIndex Score
0
Cited by
0
References
0
Claims

Abstract

An organometallic compound represented by Formula 1: M(L 1 ) n1 (L 2 ) n2   Formula 1 wherein in Formula 1, M, L 1 , L 2 , n 1 , and n 2 are the same as described in the specification.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
         1 . An organometallic compound represented by Formula 1: 
       
         
           
           
               
               
           
         
         wherein in Formulae 1 to 3, 
         M is Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, or Tm; 
         L 1  is selected from ligands represented by Formula 2; 
         L 2  is selected from ligands represented by Formula 3; 
         n1 and n2 are each independently 1 or 2, provided that a sum of n1 and n2 is 2 or 3; 
         when n1 is 2, two or more groups L 1  are identical to or different from each other, and when n2 is 2, two or more groups L 2  are identical to or different from each other; 
         R 1  to R 7 , Z 1 , and Z 2  are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60  alkyl group, a substituted or unsubstituted C 2 -C 60  alkenyl group, a substituted or unsubstituted C 2 -C 60  alkynyl group, a substituted or unsubstituted C 1 -C 60  alkoxy group, a substituted or unsubstituted C 3 -C 10  cycloalkyl group, a substituted or unsubstituted C 1 -C 10  heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10  cycloalkenyl group, a substituted or unsubstituted C 1 -C 10  heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60  aryl group, a substituted or unsubstituted C 6 -C 60  aryloxy group, a substituted or unsubstituted C 6 -C 60  arylthio group, a substituted or unsubstituted C 1 -C 60  heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 ); 
         at least one of R 1  to R 7  is a C 1 -C 4  alkoxy group substituted with at least one —F; 
         a and b are each independently selected from an integer of 1 to 4; 
         CY 1  and CY 2  are each independently a C 1 -C 60  heterocyclic group having at least one nitrogen as a ring-forming atom; 
         Y 1  and Y 2  are each independently C or N; 
         N and Y 1  are linked with each other by a single bond or a double bond, and N and Y 2  are linked with each other by a single bond or a double bond; 
         * and *′ indicate a binding site to M in Formula 1; 
         at least one of substituents of the substituted C 1 -C 60  alkyl group, the substituted C 2 -C 60  alkenyl group, the substituted C 2 -C 60  alkynyl group, the substituted C 1 -C 60  alkoxy group, the substituted C 3 -C 10  cycloalkyl group, the substituted C 1 -C 10  heterocycloalkyl group, the substituted C 3 -C 10  cycloalkenyl group, the substituted C 1 -C 10  heterocycloalkenyl group, the substituted C 6 -C 60  aryl group, the substituted C 6 -C 60  aryloxy group, the substituted C 6 -C 60  arylthio group, the substituted C 1 -C 60  heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from 
         a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, and a C 1 -C 60  alkoxy group; 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, and a C 1 -C 60  alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10  cycloalkyl group, a C 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 1 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), and —B(Q 16 )(Q 17 ); 
         a C 3 -C 10  cycloalkyl group, a C 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 1 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; 
         a C 3 -C 10  cycloalkyl group, a C 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 1 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 1 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 21 )(Q 22 ), —Si(Q 23 )(Q 24 )(Q 25 ), and —B(Q 26 )(Q 27 ); and 
         —N(Q 31 )(Q 32 ),  - Si(Q 33 )(Q 34 )(Q 35 ) and  - B(Q 36 )(Q 37 ), 
         wherein Q 1  to Q 7 , Q 11  to Q 17 , Q 21  to Q 27 , and Q 31  to Q 37  are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 3 -C 10  cycloalkyl group, a C 1 -C 10  heterocycloalkyl group, a C 3 -C 10  cycloalkenyl group, a C 1 -C 10  heterocycloalkenyl group, a C 6 -C 60  aryl group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 1 -C 60  heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. 
       
     
     
         2 . The organometallic compound of  claim 1 , wherein n1 is 2 and n2 is 1. 
     
     
         3 . The organometallic compound of  claim 1 , wherein
 R 1  to R 7 , Z 1 , and Z 2  are each independently selected from   a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20  alkyl group, and a C 1 -C 20  alkoxy group;   a C 1 -C 20  alkyl group and a C 1 -C 20  alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;   a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;   a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ); and   —Si(Q 3 )(Q 4 )(Q 5 ),   wherein Q 3  to Q 5  and Q 33  to Q 35  are each independently selected from a hydrogen, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.   
     
     
         4 . The organometallic compound of  claim 1 , wherein
 R 1  to R 7 , Z 1 , and Z 2  are each independently selected from   a hydrogen, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group;   a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of —F, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ) ;  and   —Si(Q 3 )(Q 4 )(Q 5 ),   wherein Q 3  to Q 5  and Q 33  to Q 35  are each independently selected from a hydrogen, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.   
     
     
         5 . The organometallic compound of  claim 1 , wherein
 R 2  is a hydrogen;   R 1  is a hydrogen;   both R 1  and R 2  are a hydrogen; or   neither R 1  nor R 3  are a hydrogen.   
     
     
         6 . The organometallic compound of  claim 1 , wherein at least one of R 1  to R 7  is selected from —OCH 2 F, —OCHF 2 , —OCF 3 , —OC 2 H 4 F, OC 2 H 3 F 2 , —OC 2 H 2 F 3 , —OC 2 HF 4 , OC 2 F 5 , —OC 3 H 6 F, —OC 3 H 5 F 2 , —OC 3 H 4 F 3 , —OC 3 H 3 F 4 , —OC 3 H 2 F 5 , —OC 3 HF 6 , —OC 3 F 7 , —OC 4 H 8 F, —OC 4 H 7 F 2 , —OC 4 H 6 F 3 , —OC 4 H 5 F 4 , —OC 4 H 4 F 5 , —OC 4 H 3 F 6 , —OC 4 H 2 F 7 , —OC 4 HF 8 , and —OC 4 F 9 . 
     
     
         7 . The organometallic compound of  claim 1 , wherein
 R 6  is a C 1 -C 4  alkoxy group substituted with at least one —F;   R 5  is a C 1 -C 4  alkoxy group substituted with at least one —F;   R 4  is a C 1 -C 4  alkoxy group substituted with at least one —F; or   R 4  and R 6  are each independently a C 1 -C 4  alkoxy group substituted with at least one —F.   
     
     
         8 . The organometallic compound of  claim 1 , wherein CY 1  and CY 2  are each independently a pyrrole, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isooxazole, a triazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a benzoimidazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a benzofuropyridine, or a benzothienopyridine. 
     
     
         9 . The organometallic compound of  claim 1 , wherein CY 1  is a triazole, an imidazole, or a pyrazole, and CY 2  is a pyridine, a pyrimidine, a triazine, a benzofuropyridine, or a benzothienopyridine. 
     
     
         10 . The organometallic compound of  claim 1 , wherein L 1  is selected from ligands represented by Formulae 2-1 to 2-4: 
       
         
           
           
               
               
           
         
         wherein in Formulae 2-1 to 2-4, 
         R 1  to R 3  are each independently selected from 
         a hydrogen, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group; and 
         a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of —F, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ) ;  and 
         R 4  to R 6  are each independently a C 1 -C 4  alkoxy group substituted with at least one —F. 
       
     
     
         11 . The organometallic compound of  claim 1 , wherein L 1  is selected from ligands represented by Formula 2(1): 
       
         
           
           
               
               
           
         
         wherein in Formula 2(1), 
         R 1 , R 2 , R 4  to R 7 , and R 11  to R 15  are each independently selected from 
         a hydrogen, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group; and 
         a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of —F, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ), 
         wherein at least one of R 4  to R 7  is each independently a C 1 -C 4  alkoxy group substituted with at least one —F; and 
         * and *′ indicate a binding site to M. 
       
     
     
         12 . The organometallic compound of  claim 1 , wherein L 2  is selected from ligands represented by Formula 3(1): 
       
         
           
           
               
               
           
         
         wherein in Formula 3(1), 
         X 1  is N or C(Z 11 ); X 2  is N or C(Z 12 ); X 3  is N or C(Z 13 ); X 4  is N or C(Z 14 ); X 5  is N or C(Z 15 ); X 6  is N or C(Z 16 ); and X 7  is N or C(Z 17 ); and 
         Z 11  to Z 13  are the same as Z 1 , and Z 14  to Z 17  are the same as Z 2 . 
       
     
     
         13 . The organometallic compound of  claim 12 , wherein Z 11  to Z 17  are each independently selected from
 a hydrogen, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group; and   a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of —F, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ).   
     
     
         14 . The organometallic compound of  claim 1 , wherein L 2  in Formula 1 is selected from ligands represented by Formulae 3-1 to 3-30: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein in Formulae 3-1 to 3-30, 
         Z 1  and Z 2  are each independently selected from 
         a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20  alkyl group, and a C 1 -C 20  alkoxy group; 
         a C 1 -C 20  alkyl group and a C 1 -C 20  alkoxy group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group; 
         a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group; 
         a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ) ;  and 
         —Si(Q 3 )(Q 4 )(Q 5 ); 
         wherein Q 3  to Q 5  and Q 33  to Q 35  are each independently selected from a hydrogen, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, and 
         wherein 
         b4 is 1,2,3, or4, 
         b3 is 1,2, or3, 
         a2 and b2 are each independently 1 or 2; and 
         * and *′ indicates a binding site to M in Formula 1. 
       
     
     
         15 . The organometallic compound of  claim 14 , wherein Z 1  and Z 2  are each independently selected from
 a hydrogen, —F, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group;   a methyl group, an ethyl group, a propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decanyl group, an isodecanyl group, a sec-decanyl group, a tert-decanyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, each substituted with at least one of —F, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, and —Si(Q 33 )(Q 34 )(Q 35 ); and   —Si(Q 3 )(Q 4 )(Q 5 ),   wherein Q 3  to Q 5  and Q 33  to Q 35  are each independently selected from a hydrogen, a C 1 -C 20  alkyl group, a C 1 -C 20  alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group.   
     
     
         16 . The organometallic compound of  claim 1 , wherein the organometallic compound is one of Compounds 1 to 35: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         17 . An organic light-emitting device comprising:
 a first electrode;   a second electrode; and   an organic layer disposed between the first electrode and the second electrode,   wherein the organic layer comprises an emission layer and the organometallic compound of  claim 1 .   
     
     
         18 . The organic light-emitting device of  claim 17 , wherein
 the first electrode is an anode,   the second electrode is a cathode, and   the organic layer comprises:
 i) a hole transport region disposed between the first electrode and the emission layer, wherein the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer; and 
 ii) an electron transport region that is disposed between the emission layer and the second electrode, wherein the electron transporting region comprises at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. 
   
     
     
         19 . The organic light-emitting device of  claim 17 ,
 wherein the emission layer comprises the organometallic compound of  claim 1 ,   wherein the emission layer further comprises a host, and   wherein an amount of the organometallic compound in the emission layer is less than an amount of the host.

Join the waitlist — get patent alerts

Track US2018301640A9 — get alerts on status changes and closely related new filings.

We store only your email — no account needed. See our privacy policy.